Hydrochloric Acid → HCID 178437425, compound

HRID 2260560Notes

Reaction equation

HRID 2260560 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[N:32]=[N:33][N:34](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:35]=2)[CH:19]=[CH:18]3)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].Cl.[OH-].[Na+].O>CO>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)[CH:19]=[CH:18]3)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22915620HCID 22915620, compound

Product 1

HCID 178437425HCID 178437425, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

852 mg (1.21 mmol) of 2-ethyl-5,7-dimethyl-3-{[2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]quinolin-6-yl]methyl}-3H-imidazo[4.5-b]pyridine obtained in Example 14 was suspended in 12 ml of methanol and 12 ml of concentrated hydrochloric acid were added thereto over an iced water bath. After stirring at room temperature for 24 hours, the reaction mixture were cooled with ice and acidified with a 10N sodium hydroxide solution. 10 ml of water were added thereto followed by filtration and the filter cake was washed with 10 ml of a 1N sodium hydroxide solution. The filtrate was acidified by adding concentrated hydrochloric acid dropwise thereto with stirring and then extracted with 100 ml of ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 518 mg of 2-ethyl-5,7-dimethyl-3-{[2-[2-(1H-tetrazol-5-yl)phenyl]quinolin-6-yl]methyl}-3 H-imidazo[4,5-b]pyridine.

Workup

  1. temperaturethe reaction mixture were cooled with ice
  2. filtrationthereto followed by filtration
  3. washthe filter cake was washed with 10 ml of a 1N sodium hydroxide solution
  4. additionby adding concentrated hydrochloric acid dropwise
  5. stirringwith stirring
  6. extractionextracted with 100 ml of ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1a76df8cf56147ae876b0f87b461ce67
Source dataset
uspto-grants-1995_12
Patent number
US05478832

Reaction notes

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